ethyl-but-3-ynyl ether | 26976-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl-but-3-ynyl ether
• 英文别名: Aethyl-but-3-inyl-aether；4-Aethoxy-butin-(1)；Ethyl(3-butynyl) ether；4-ethoxybut-1-yne
• CAS: 26976-26-1
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: WAPNRRHIEGNDKL-UHFFFAOYSA-N

物化性质

• 沸点：
  109.9±23.0 °C(Predicted)
• 密度：
  0.833±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-iodoquinolin-3-ol 、 ethyl-but-3-ynyl ether 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以77%的产率得到2-(2-ethoxyethyl)furo[2,3-c]quinoline
  参考文献：
  名称：

  Exquisite Selectivity for Human Toll-Like Receptor 8 in Substituted Furo[2,3-c]quinolines

  摘要：

  Toll-like receptor (TLR)-8 agonists activate adaptive immune responses by inducing robust production of T helper 1-polarizing cytokines, suggesting that TLR8-active compounds may be promising candidate adjuvants. We synthesized and evaluated hitherto unexplored furo[2,3-d]quinolines and regioisomeric furo[3,2-c]quinolines derived via a tandem, one-pot Sonogashira coupling and intramolecular 5-endo-dig cyclization strategy in a panel of primary screens. We observed a pure TLR8-agonistic activity profile in select furo[2,3-c]quinolines, with maximal potency conferred by a C2-butyl group (EC50 = 1.6 mu M); shorter, longer, or substituted homologues as well as compounds bearing C1 substitutions were inactive, which was rationalized by docking studies using the recently described crystal structure of human TLR8. The best-in-class compound displayed,prominent proinflammatory cytokine induction (including interleukin-12 and interleukin-18), but was bereft of interferon-alpha inducing properties, confirming its high selectivity for human TLR8.

  DOI：

  10.1021/jm400694d
• 作为产物：
  描述：

  2-溴乙基乙基醚 、 乙炔钠 在 氨 作用下， 生成 ethyl-but-3-ynyl ether
  参考文献：
  名称：

  Some Ethers of 3-Butyn-1-ol¹

  摘要：

  DOI：

  10.1021/ja01280a053

文献信息

• Bertrand,M.-T. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1975, vol. 280, p. 999 - 1002
  作者：Bertrand,M.-T. et al.

  DOI：——

  日期：——
• BERTRAND M.-T.; COURTOIS G.; MIGINIAC L., C. R. ACAD. SCI. <CHDC-AQ>, 1975, C280, NO 15, 999-1002
  作者：BERTRAND M.-T.、 COURTOIS G.、 MIGINIAC L.

  DOI：——

  日期：——
• Some Ethers of 3-Butyn-1-ol¹
  作者：P. A. McCusker、J. W. Kroeger

  DOI：10.1021/ja01280a053

  日期：1937.1
• Exquisite Selectivity for Human Toll-Like Receptor 8 in Substituted Furo[2,3-<i>c</i>]quinolines
  作者：Hari Prasad Kokatla、Diptesh Sil、Subbalakshmi S. Malladi、Rajalakshmi Balakrishna、Alec R. Hermanson、Lauren M. Fox、Xinkun Wang、Anshuman Dixit、Sunil A. David

  DOI：10.1021/jm400694d

  日期：2013.9.12

  Toll-like receptor (TLR)-8 agonists activate adaptive immune responses by inducing robust production of T helper 1-polarizing cytokines, suggesting that TLR8-active compounds may be promising candidate adjuvants. We synthesized and evaluated hitherto unexplored furo[2,3-d]quinolines and regioisomeric furo[3,2-c]quinolines derived via a tandem, one-pot Sonogashira coupling and intramolecular 5-endo-dig cyclization strategy in a panel of primary screens. We observed a pure TLR8-agonistic activity profile in select furo[2,3-c]quinolines, with maximal potency conferred by a C2-butyl group (EC50 = 1.6 mu M); shorter, longer, or substituted homologues as well as compounds bearing C1 substitutions were inactive, which was rationalized by docking studies using the recently described crystal structure of human TLR8. The best-in-class compound displayed,prominent proinflammatory cytokine induction (including interleukin-12 and interleukin-18), but was bereft of interferon-alpha inducing properties, confirming its high selectivity for human TLR8.